EP3044258B1 - Compositions réticulables par peroxyde et leurs procédés de production - Google Patents

Compositions réticulables par peroxyde et leurs procédés de production Download PDF

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Publication number
EP3044258B1
EP3044258B1 EP14767259.6A EP14767259A EP3044258B1 EP 3044258 B1 EP3044258 B1 EP 3044258B1 EP 14767259 A EP14767259 A EP 14767259A EP 3044258 B1 EP3044258 B1 EP 3044258B1
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EP
European Patent Office
Prior art keywords
peroxide
tac
dstdp
pellets
molecular weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP14767259.6A
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German (de)
English (en)
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EP3044258A1 (fr
Inventor
Manish TALREJA
Jeffrey M. Cogen
Gerrit GROOT-ENZERNIK
Timothy J. Person
Neil W. Dunchus
Gary W. BUCKLER
Gabriele Goethel
Saurav S. Sengupta
Antoni ADAMCAZYK
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Dow Global Technologies LLC
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Dow Global Technologies LLC
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Priority to EP17183592.9A priority Critical patent/EP3257892B1/fr
Publication of EP3044258A1 publication Critical patent/EP3044258A1/fr
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Publication of EP3044258B1 publication Critical patent/EP3044258B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/372—Sulfides, e.g. R-(S)x-R'
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/14—Peroxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
    • H01B13/06—Insulating conductors or cables
    • H01B13/14—Insulating conductors or cables by extrusion
    • H01B13/148—Selection of the insulating material therefor
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/308—Wires with resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring

Definitions

  • compositions, process, etc. is not limited to the components, steps, etc. disclosed, but rather can include other, undisclosed components, steps, etc.
  • the term “consisting essentially of” excludes from the scope of any composition, process, etc. any other component, step etc. excepting those that are not essential to the performance, operability or the like of the composition, process, etc.
  • the term “consisting of' excludes from a composition, process, etc., any component, step, etc. not specifically disclosed.
  • melt and like terms mean a solid composition in a molten state.
  • a melt may or may not comprise gels and/or solid particulates.
  • low molecular weight means non-polymeric, non-oligomeric and/or of a molecular weight not in excess of 1400 grams per mole (g/mol), preferably not in excess of 1000 g/mol and more preferably not in excess of 750g/mol.
  • low melting means a melting temperature not in excess of 95°C, preferably not in excess of 90°C and more preferably not in excess of 85°C, as measured by peak melting point using DSC.
  • Example 1 When the AO mixture and TAC are pre-blended in a 1:1 ratio in Example 1, surprisingly, no trace of peak 3 is observed, while there is no significant effect (apart from dilution) on the other peaks (1, 2, and 4).
  • Example 1 therefore only has two peaks: peak 5 which comes from the AO mixture (similar to peak 1) and peak 6 which is a combination of peaks 2 and 4. This result is clearly shown in Figure 1 where all three thermograms are collated. Peak 3 in the TAC thermogram is a highly exothermic sharp peak indicating a safety hazard and a potential for explosion.
  • the inventive mixture of Example 1 completely annihilates this peak (reaction), significantly improving the safety.
  • Table 8 compares the MDR-Mh values over four weeks of aging at 70°C for TINUVINTM 622 introduced via compounding and soaking.
  • Figure 4 presents this cure retention data by normalizing the MDR-Mh values of an aged sample with its day zero (initial) MDR-Mh.
  • Table 8 and Figure 4 clearly indicate that TINUVINTM 622 when introduced via soaking, leads to loss in cure faster than when introduced via compounding.
  • low molecular weight bases are required for soaking to be effective and enable one to circumvent the screen build up encountered with prior art high molecular weight high melting HALS.
  • Pilot plant experiments are run on a ZSK-30 twin screw extruder to simulate the screen build up in an actual production plant.
  • Higher additive loadings (six times the baseline formulation 1 loadings: 1.37 wt% DSTDP + 0.83 wt% CYANOXTM 1790) are used for these experiments to accelerate the screen build up.
  • Experiments are run at 245 °C.
  • a stack of screens ranging from 23 ⁇ m opening to 200 ⁇ m opening is used. Post-extrusion, the screen packs are delaminated, polymer is removed by toluene wash, and build up is measured by immersing the 23 ⁇ m opening screen in water and weighing the water soluble extract.
  • Table 10 shows the build up on the screens in terms of mg of water soluble extract for inventive (post-extrusion soaked lower molecular weight bases) and comparative (compounded) examples.
  • Table 10 Build up on the Screens Measured as Water-Soluble Extract in mg for Formulations Run in Pilot Plant on Twin Screw ZSK-30 Extruder Formulation mg of extract Post Extrusion Soaked low mwt bases (inventive) 1.37% DSTDP + 0.83% C1790 + 0.0344% TAC (TAC soaked post extrusion) 0.15 1.37% DSTDP + 0.83% C1790 + 0.0344% T765 (T765 soaked post extrusion) 0.15 Compounded bases (comparative) 1.37% DSTDP + 0.83% C1790 + 0.0344% TAC compounded 0.60 1.37% DSTDP + 0.83% C1790 + 0.0344% T765 compounded 0.50 1.37% DSTDP + 0.83% C1790 + 0.0344% C3346 compounded 1.10

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Physics & Mathematics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Organic Insulating Materials (AREA)
  • Insulated Conductors (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
  • Extrusion Moulding Of Plastics Or The Like (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Claims (15)

  1. Une composition de pré-mélange homogène comprenant de 0,6 à 66 % en poids (% en poids) de cyanurate de triallyle (TAC) et de 34 à 99,4 % en poids d'un antioxydant (AO).
  2. La composition de la revendication 1 dans laquelle le TAC et l'AO sont présents selon un rapport en poids TAC/AO allant de 1/100 à 3/2.
  3. Une composition réticulable par peroxyde comprenant :
    (A) un polymère réticulable par peroxyde ;
    (B) un peroxyde ;
    (C) du cyanurate de triallyle (TAC) ; et
    (D) un ou plusieurs antioxydants (AO),
    le TAC présent à une concentration allant de 0,0005 % à 0,01 %.
  4. La composition de la revendication 3 sous forme d'une pastille.
  5. Un procédé pour fabriquer une pastille réticulable par peroxyde, le procédé comprenant les étapes consistant à :
    (1) former un produit fondu homogène :
    (A) d'un polymère réticulable par peroxyde ; et
    (B) d'un pré-mélange homogène de cyanurate de triallyle (TAC) et d'AO, le pré-mélange homogène comprenant ou consistant essentiellement en 0,6 à 66 % en poids de TAC et 34 à 99,4 % en poids d'AO ;
    (2) faire passer le produit fondu homogène de (1) à travers un filtre avec une ouverture de maille inférieure à 100 µm ; et
    (3) former des pastilles à partir du produit fondu homogène filtré de (2).
  6. Le procédé de la revendication 5 comprenant l'étape supplémentaire consistant à imprégner des pastilles avec un peroxyde.
  7. Une composition réticulable par peroxyde comprenant :
    (A) un polymère réticulable par peroxyde ;
    (B) une base de faible masse moléculaire, ou à faible point de fusion, ou d'azote liquide à hauteur de 0,0005 % à 0,01 % ;
    (C) un ou plusieurs antioxydants (AO) ; et
    (D) facultativement, un peroxyde.
  8. La composition de la revendication 7 dans laquelle la base comprend du TAC et/ou du N,N'-1,6-hexanediylbis(N-(2,2,6,6-tétraméthyl-4-pipéridinyle)-formamide et/ou un mélange de bis(1,2,2,6,6-pentaméthyl-1-pipéridyle)sébacate et de méthyl 1,2,2,6,6-pentaméthyl-4-pipéridyle sébacate.
  9. La composition de la revendication 7 dans laquelle l'antioxydant comprend du DSTDP.
  10. Un procédé pour fabriquer une pastille réticulable par peroxyde, le procédé comprenant les étapes consistant à :
    (1) former un produit fondu homogène :
    (A) d'un polymère réticulable par peroxyde ;
    (B) d'une base de faible masse moléculaire, ou à faible point de fusion, ou d'azote liquide à hauteur de 0,0005 % à 0,01 %, et
    (C) facultativement, un antioxydant (AO) ;
    (2) faire passer le produit fondu homogène de (1) à travers un filtre avec une ouverture de maille inférieure à 100 µm ; et
    (3) former des pastilles à partir du produit fondu homogène filtré de (2).
  11. La procédé de la revendication 10 comprenant l'étape supplémentaire consistant à imprégner les pastilles avec un peroxyde.
  12. Un procédé pour fabriquer une pastille réticulable par peroxyde, le procédé comprenant les étapes consistant à :
    (1) former un produit fondu d'un polymère réticulable par peroxyde avec un AO ;
    (2) faire passer le produit fondu de (1) à travers un filtre avec une ouverture de maille inférieure à 100 µm ;
    (3) former des pastilles à partir du produit fondu homogène filtré de (2) ; et
    (4) imprégner les pastilles avec une base à faible masse moléculaire ou d'azote liquide.
  13. Le procédé de la revendication 12 dans lequel les pastilles sont également imprégnées avec un peroxyde.
  14. Un câble ou fil métallique comprenant une gaine fabriquée selon l'un quelconque des procédés des revendications 5 à 7 et 10 à 13.
  15. Un câble ou fil métallique comprenant une gaine comprenant l'une quelconque des compositions des revendications 1 à 4 et 8 à 9.
EP14767259.6A 2013-09-13 2014-09-08 Compositions réticulables par peroxyde et leurs procédés de production Active EP3044258B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP17183592.9A EP3257892B1 (fr) 2013-09-13 2014-09-08 Compositions réticulables par peroxyde et leurs procédés de production

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361877405P 2013-09-13 2013-09-13
PCT/US2014/054526 WO2015038467A1 (fr) 2013-09-13 2014-09-08 Compositions réticulables par peroxyde et leurs procédés de production

Related Child Applications (2)

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EP17183592.9A Division EP3257892B1 (fr) 2013-09-13 2014-09-08 Compositions réticulables par peroxyde et leurs procédés de production
EP17183592.9A Division-Into EP3257892B1 (fr) 2013-09-13 2014-09-08 Compositions réticulables par peroxyde et leurs procédés de production

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EP3044258A1 EP3044258A1 (fr) 2016-07-20
EP3044258B1 true EP3044258B1 (fr) 2017-09-06

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US (3) US9745447B2 (fr)
EP (2) EP3044258B1 (fr)
JP (3) JP6539277B2 (fr)
KR (1) KR102181768B1 (fr)
CN (2) CN107245163B (fr)
BR (1) BR112016004083B1 (fr)
CA (1) CA2922839C (fr)
MX (1) MX2016002710A (fr)
TW (1) TWI653272B (fr)
WO (1) WO2015038467A1 (fr)

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JP2016540098A (ja) 2016-12-22
JP6539277B2 (ja) 2019-07-03
TW201518367A (zh) 2015-05-16
KR20160054515A (ko) 2016-05-16
CN105492518B (zh) 2018-07-24
US10221299B2 (en) 2019-03-05
MX2016002710A (es) 2016-05-10
EP3257892B1 (fr) 2021-09-01
CN107245163B (zh) 2019-09-24
JP6811216B2 (ja) 2021-01-13
CN105492518A (zh) 2016-04-13
CA2922839C (fr) 2021-10-26
TWI653272B (zh) 2019-03-11
US20170327666A1 (en) 2017-11-16
CN107245163A (zh) 2017-10-13
EP3257892A1 (fr) 2017-12-20
JP7142616B2 (ja) 2022-09-27
US10577482B2 (en) 2020-03-03
KR102181768B1 (ko) 2020-11-25
WO2015038467A1 (fr) 2015-03-19
BR112016004083B1 (pt) 2021-04-27
JP2020033562A (ja) 2020-03-05
JP2018204028A (ja) 2018-12-27
US20190040231A1 (en) 2019-02-07
US20160208079A1 (en) 2016-07-21
EP3044258A1 (fr) 2016-07-20
US9745447B2 (en) 2017-08-29
CA2922839A1 (fr) 2015-03-19

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